When he announced his running prior to 2016, I thought it was a joke.
The apprentice guy? I was born in 92 and really just hardly aware of him except for the apprentice, of which I only watched a few of the celebrity apprentice episodes because it had celebrities on that I liked such as Gilbert Gottfried and Penn Jillette.
So I didn't really care for Trump for two reasons.
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I associated him with reality TV and I did and still do despise reality TV. I saw it and still see it as one of those things that decayed the American culture.
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When he was the subject of a comedy central roast around the time he announced he was running, he didn't seem like he could take a joke.
I've since seen that Trump's not the type of guy who does big hearty showy laughs. If he's amused by something he'll just sort of smile. But at the time, I didn't think he had a sense of humor about himself, and I've always been someone who's wary of people who can't take jokes about themselves.
But what changed for me officially was when I saw a video of his, one of his campaign videos addressing the problem of political correctness in the culture and stifling free speech.
That alone was enough to ensure I was behind him 100%. I never saw any other "conservative" politician boldly address this issue or even address it at all really.
Mostly it was just us on the internet fighting the culture war who bothered to address and fight political correctness. Where was John McCain's take down of PC culture? Where was Mitt Romney's takedown of PC culture? But here, the guy who I thought was just doing this for attention as a reality TV guy, is the only one to flat-out say, political correctness is a problem and needs to be addressed.
So that video made me a Trump supporter. Then seeing how the mainstream media treated the man made me see things even clearer.
I never was really a fan of Trump. I never watched the Apprentice or anything he was involved in. I was aware OF him, because being in NJ/NYC you knew who he was.
When he ran in 2016 I also thought it was ridiculous. I was 100% behind Rand Paul, with maybe Ted Cruz as a 2nd option. (Jeb! would have made me vote third party) However, once Rand dropped out, and after seeing Trumps debates, and his actual positions on issues. I came around pretty fast. When it was down to just Trump, Cruz, and that Ohio Gov who's name I forget (and don't feel like googling) I was fully 100% on board with Trump. (Still did like Cruz though)
What sold me on Trump was actually listening to HIM and not reading what the media said about him. I've been onboard ever since. I've donated and voted for him three times.